


Not So Timid After All

by lydslibrary



Category: Supernatural
Genre: Dean Winchester Smut, Dom Dean Winchester, Dom/sub, F/M, Oral Sex, Rough Oral Sex, Rough Sex, SPN Smut, Supernatural smut, sub Reader
Language: English
Status: Completed
Published: 2020-07-24
Updated: 2020-07-24
Packaged: 2021-03-04 17:55:56
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,137
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25490503
Author URL: https://archiveofourown.org/users/lydslibrary/pseuds/lydslibrary
Summary: You’ve had a crush on Dean Winchester for years but are far too shy to make a move. When you’re working a case with Dean at a costume party, he decides to make a move instead. Turns out, you’re not so shy in the bedroom.
Relationships: Dean Winchester/Reader
Comments: 3
Kudos: 72





	Not So Timid After All

**Author's Note:**

> This was a request I did for someone on Tumblr!
> 
> The request: Smut between Dean and a nerdy/timid reader. She’s a hunter living with the boys for some years and secretly has a crush on Dean. For a hunt, they need to go to a costume party, so the reader dresses up as Marilyn Monroe and Dean is lusting badly for her, finally getting a glimpse of her body since she’s always in baggy, casual clothes. Ends up in kinky smut since she’s secretly a sub.

“Hey, Y/N, we caught a case, if you want to join,” Dean said as he popped his head into your room. You looked up from the book you were reading.

“What is it?” You asked.

“A ghost we think, but get this, the place it’s haunting… there’s a costume party there tonight… and it’s freakin’ Halloween,” Dean said enthusiastically, a smile spreading across his face. You raised your eyebrows at him.

“Hmm…,” you thought, thinking about any costumes you might have on hand. One came to mind, but you weren’t sure that you were ready to flaunt everything you had in front of the boys, Dean especially. You had been living in the bunker with them for a few years now but you can’t remember a time that they’ve ever seen you dressed up.

“C’mon, it’ll be fun! I mean, it’s the perfect case. A ghost at a costume party!? On Halloween night!?” Dean rambled on. You watched him fondly. You’ve had somewhat of a crush on the older Winchester for years now, but you were very shy, you kept to yourself, and you could never imagine that Dean would think of you in any other way than just a friend. Besides, you had far more in common with Sam when it came to interests anyway.

“What are you going as?” You asked, already knowing the answer. _A cowboy_.

“You have to ask? A cowboy, obviously. It’s like you don’t even know me,” Dean said sarcastically as he shook his head. You rolled your eyes.

“Alright, I’m in I guess,” you said nonchalantly, focusing back on your book.

“Sweet, well, better start getting ready then, it’s about an hour drive.” Dean left, closing the door behind him. You sighed and put your book down on your chest. You had one costume that you wore to a costume party years ago; Marilyn Monroe. You got up from your bed and walked over to your dresser, rummaging through drawers before you finally saw the fabric of the white dress stuffed underneath some of your regular baggy clothes at the back of a drawer. You pulled it out and held it in front of you, staring at it. You couldn’t remember the last time you wore a dress. You found the remaining bits of the old costume in various parts of your room; the wig in a box under your bed, the heels in a pile of all your shoes that sat in the corner of the room. Once you had everything together, you laid it all out in front of you. You loved dressing up, but you weren’t the most outgoing person. For some reason, you felt nervous about Dean seeing you in this get-up, and you didn’t know why. You put on the costume piece by piece, and after brushing out the wig and styling it the classic Marilyn Monroe way and putting on some makeup, you looked at yourself in the mirror and smiled. You hadn’t felt this good about yourself in a while; wearing things that accented your breasts and curves, heels, makeup… it wasn’t something that you ever did, especially since becoming a hunter. “Y/N, we’re ready whenever you are!” You heard Dean’s voice echo throughout the bunker. You gave yourself a confident nod in the mirror and headed out of your room to meet the brothers in the war room.

“How are you not more excited about this, Sammy? Are you kidding me, it’s like the perfect –,” Dean stopped talking to his brother when he caught a glimpse of you walking in.

“What?” You asked him innocently, grabbing your purse off the table.

“N-nothing… I’ve just, uh, always had a crush on Marilyn Monroe,” Dean explained, stuttering a little. You looked at him suspiciously.

“Right… anyway, you guys good to go?” You questioned, looking at the two brothers standing before you. Dean was dressed in the exact get-up he said he’d be dressed in; he looked like he’d been plucked right out of some classic Western film. Sam, on the other hand… “I see you’re going as a lumberjack, then?” You teased, noticing that Sam had refused to dress up and was wearing the usual plaid button up. Sam gave you an irritated look and Dean chuckled softly.

“We’re working on a case, guys. I mean, c’mon, is it really practical to fight a ghost dressed in,” Sam motioned to you and Dean’s costumes, “cowboy boots and a dress?”

“What I wear doesn’t determine my hunting skills, Sam. Anything you can do I can do in heels and a damn dress,” you said with confidence and turned to walk up the stairs. The brothers glanced at each other with their eyebrows raised and then watched you walk to the bunker’s exit; this was not the quiet and timid Y/N that they were used to. The costume was giving you some of Marilyn’s confidence, and you weren’t complaining.

You felt Dean’s eyes on you for most of night and even caught him licking his lips a few times out of the corner of your eye. You didn’t know how to react, although the way Dean was looking at you made you want every dirty fantasy you’d ever had about him to come true.

“You guys look upstairs, I’ll check out the rest of the party, see of anyone’s noticed anything,” Sam suggested, after about an hour of wandering aimlessly through the crowd. The party was in a giant mansion, the music was blaring, and there wasn’t exactly much light in the place; all things which made working this case a little harder. You and Dean headed towards the staircase, which, of course, was roped off to guests, but hey, breaking the rules was in your job description. The bad lighting and loud music made escaping off to the top floor an easy job, and you and Dean began scouring the hallways, flashlights and EMF meters in hand.

“Hey,” Dean whispered from behind you. You turned around. “Let’s check out in here,” he said, motioning towards a door beside him.

“Why?” You asked, confused because you didn’t feel, see, or hear anything coming from behind the door that would remotely suggest a ghost, or anything at all for that matter.

“Just – c’mon,” Dean said, opening the door quietly. He shined his flashlight into the room; a bedroom, and a huge one at that. Probably one of many.

“Dean, what if someone comes in,” you whispered nervously.

“Eh, I’m sure they’re preoccupied with the party,” he said, searching the wall for a light switch. He switched it on when he found it, closing the door and turning around to face you. He took off his cowboy hat and placed it on a nearby chair.

“Dean, what are you –”

Dean was inches away from your face before you could finish. “Correct me if I’m wrong, Y/N, but you like me, yeah? Like, _like, like_ me?” You gulped.

“Uh, well –”

“Because Sammy’s been puttin’ all these ideas in my head ‘bout you… so if he’s wrong, I’ll kill him for makin’ me look stupid right now.”

“Sam told you something?” You asked, mortified. You never told Sam exactly how you felt about Dean, but you did drop subtle hints… which you now realized probably weren’t so subtle.

“Not anything specific, he just… made me open my eyes to how you act around me, y’know.”

“And how do I act around you, Dean?”

He curved his lips into a smirk. “Like you want me to fuck you.”

You swallowed again. It was true, but you couldn’t believe that Dean had actually noticed.

“See, I didn’t see it before, when you first moved in, and then Sammy started pointin’ things out to me, things that you only do around me, and then suddenly you weren’t innocent little Y/N in my eyes anymore. And I… I was never sure, until tonight. The way you kept lookin’ at me whenever I’d look at you,” Dean started dragging his fingertips down your arm, causing you to shiver, and leaned in close to your ear, his stubble rough against your cheek, “Yeah, that told me all I needed to know. And I’m willing to bet you’re not as timid in the bedroom as you are outside of it, hm?” Dean whispered. You took a deep breath. You couldn’t wrap your head around what was occurring, it didn’t feel real. “Answer me,” Dean growled. The heat between your legs began to rise.

“Y-yes,” you breathed. Dean smiled devilishly.

“Mm, I thought so. I’ve always thought you were so beautiful, Y/N, but seeing you tonight, in this… yeah, all I’ve been wanting to do since I saw you in it is rip it right off.” He hooked his fingers under the straps of your dress and slid them off your shoulders. “This is okay, right?” He whispered, pausing to make sure that you wanted this too. You nodded aggressively, still trying to process what was going on. Dean planted soft kisses down you neck and collarbone, letting go of the dress straps and allowing gravity pull the dress down your body.

“D-Dean, the c-case,” you breathed, remembering that you were in a stranger’s house that was being haunted by a ghost.

“Shhh, Sammy’s got it. Relax, Y/N, let me take care of you, hm?” You nodded softly and Dean reached around you to unclasp your bra. He watched your breasts bounce a little as he slid it off, licking his lips in a way that drove you crazy. “You’re so fuckin’ beautiful, Y/N. Why you hide all of this under those baggy clothes, I’ll never understand. Fuck, I want to do so many dirty things to you.”

“Do them, then,” you whispered, Dean’s compliments of your body giving you an extra boost of confidence. That was all Dean needed to drag you to the bed and bend you over it. He ripped off your panties and used them to tie your hands behind your back, making you squeeze your thighs together at his display of dominance. Dean leaned over you, his hands making dips in the bed on each side of your shoulders, his growing bulge pressed against your ass. You felt Dean’s stubble on your cheek again.

“You ever been tied up before, doll?” He questioned, his voice low and gruff.

You smiled to yourself. Oh, the things Dean Winchester was about to find out about you. “Yes, sir,” you responded, biting back a smirk.

“Oh?” Dean asked, surprise in his voice, “You know how to behave then?”

“Yes, sir.”

Dean moaned in approval as he trailed kisses down your spine, dropping to his knees in front of your ass. Dean tapped your ankles, signaling for you to spread your legs further, and you did, your dripping cunt coming into his view. “Don’t move. Don’t make a sound. I would hate for someone to walk in on you like this, all tied up for me,” Dean said sternly. Dean grabbed the area where your thighs met your ass cheeks and licked a stripe up your folds, making you flinch a little, but not enough for him to notice. He worked his way through your folds with his tongue, licking, flicking, and sucking all the right spots. You were clinging to the bed sheets and trying to hold still, biting back moans. Your clit was pounding and your walls were clenching around nothing, begging for something to fill the emptiness. “You’re such a good girl, Y/N,” Dean praised, as he began to circle your clit with his tongue. You almost gasped when you felt a finger enter you and start pumping in and out slowly. Your breath hitched when Dean added a finger, and you were proud of yourself for managing to be so quiet while you were experiencing something quite euphoric. This wasn’t just some random hook-up, this was Dean Winchester, your crush of the last few years, giving you the best oral you’ve ever received. Dean stood up suddenly, his fingers still inside of you, and you groaned at the absence of his tongue against your clit. The second you made a sound, you regretted it instantly, for Dean was pulling his fingers out of you and pulling you up off the bed by your upper arm. He spun you around to face him, his nose almost touching yours. “Was that a sound, Y/N?” Dean asked, his eyebrows raised. You nodded. “Use your words.”

“Yes, sir,” you gulped, wondering what he had in store for you.

“Well, I guess we’ll have to shut you up then, hm?” He growled, pulling down on your arm, signaling for you to get on your knees. You obeyed, trying not to focus on the juices dripping down your thighs. You watched as Dean sat down on the edge of the bed to take off his boots, drawing out the anticipation. He stood up and walked back over to you, stopping right in front of your face. You could see his bulge through his jeans. You watched as Dean unbuckled his obnoxious belt buckle and unzipped his jeans, wishing you could do it for him but your hands were still tied behind your back. You breathed in deeply as Dean slid off his underwear, kicking them into a corner of the room, his cock thick and hard, precum leaking from the tip. You licked your lips hungrily and opened your mouth without waiting for Dean to ask you to. Dean pumped his cock slowly in front of your face, smirking at your eagerness to taste it. You stuck your tongue out with your mouth still wide open, hoping that Dean would realize just how much you wanted his cock inside you, inside any part of you. Dean tapped the tip of his cock against your tongue a few times, allowing the saltiness of his precum to sink into your taste buds, before shoving all of himself inside you, hitting the back of your throat. You squeezed your thumb in your left fist, a trick to get rid of your gag reflex that you had learned a while ago, letting Dean repeatedly hit the back of your throat with little to no discomfort. Dean fucked your face relentlessly, until spit was dripping down the sides of your mouth and he was moaning “fuck” under his breath. You felt his cock twitch in your mouth and Dean slowed down, pulling his cock out after a few more thrusts. “Stand up, turn around,” Dean demanded, and you did as you were told. Dean quickly untied your wrists from behind your back and spun you back around, pulling you into a deep kiss; your first kiss with him. You felt butterflies in your stomach, your heart fluttered, all those movie clichés that supposedly happen when you kiss someone, happened. You thought about how backwards this all was, about how his lips should have probably come in contact with yours before his cock did, about how you were in the middle of being effortlessly dominated by him and your heart had the audacity to fucking flutter… Dean deepened the kiss, guiding you over to the bed, your thighs hitting the edge of the mattress. He pushed you down onto the bed, and you scooted up a little bit, your head resting on the pillows. Dean crawled on top of you, wasting no time with ripping his shirt off and lining his cock up with your entrance. He thrust into you with so much force, making you yelp, which resulted with his hand over your mouth as he pounded into you. “There are so many things I’d rather be doing with this hand, Y/N, but I need you to be quiet,” Dean said as he looked into your eyes. You nodded to signal that you understood and Dean moved his hand from your mouth to one of your nipples, pinching it between his fingers. After a few more thrusts Dean changed angles, sitting up straighter and pulling your legs over his shoulders, pounding even deeper into you. He grabbed the part of your thigh right above your knee with one hand, the other hand reaching around to find your clit, rubbing circles around it with his thumb when he found it. It took everything you had in you not to scream, the only thing keeping you from doing so being the fact that you were at a party… at a stranger’s house. Dean grunted as he thrusted into you a few more times and you felt the all-too familiar heat begin to rise in your abdomen as Dean kept massaging your clit. You felt Dean’s cock twitch inside of you, just as it had in your mouth, and suddenly, the familiar heat reached its boiling point, and you felt your orgasm erupt through you as you arched your back and fought back a scream. You felt Dean’s warm cum cover your stomach and you opened your eyes to watch him ride out his climax as he towered over you, head thrown back and eyes closed, pumping his cock slowly as he shuddered and moaned under his breath. He finally opened his eyes to look down at you and the mess he made. “Sorry, I, uh, didn’t have a condom,” he explained sheepishly once he finally caught his breath. You chuckled.

“That’s okay, it doesn’t bother me,” you said, earning a surprised look from him. “You keep looking at me like that.”

“Yeah, Y/N, because like… when we’re back at the bunker all you do is read and do crosswords and cute little nerdy things and you – you won’t even cuss! But here you are, sucking my cock like you have a degree in giving head and… I mean, _clearly_ you know how to be a good sub and it’s like, damn… what’s next? You like being spanked, too?”

“That’s my favorite, actually,” you said with a wink, earning you another bug-eyed stare from Dean. “I’m gonna clean this off, now.” You rolled off the bed, thanking the universe that this bedroom had a bathroom so you wouldn’t have to go looking for one, covered in cum. You grabbed your costume from the floor, surprised that you had fastened your wig to your head well enough that it hadn’t fallen off throughout all of the events that had just occurred. You got dressed and fixed yourself up in the bathroom mirror, coming back out to see a fully dressed Dean. “Back to the case, then,” you said, as though nothing had happened. Dean looked at you quizzically. “What now?” You asked.

“That… I mean, that wasn’t a one-time thing, was it?”

“No, you idiot, now let’s go. Sam probably thinks we’ve found something by now.”


End file.
